Tributylvinyltin → 3-Phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)isoxazole

HRID 1506482Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[S:10][C:9]([C:15]3[O:19][N:18]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:16]=3[C:26]([F:29])([F:28])[F:27])=[N:8][C:7]=1[CH2:6][CH2:5]2.[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:20]1([C:17]2[C:16]([C:26]([F:27])([F:28])[F:29])=[C:15]([C:9]3[S:10][C:11]4[C:12]5[C:4](=[CH:3][C:2]([CH:30]=[CH2:31])=[CH:14][CH:13]=5)[CH2:5][CH2:6][C:7]=4[N:8]=3)[O:19][N:18]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To 5-(7-bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (Preparation 82D), 0.4 g, 0.838 mmol) in toluene (2 mL) was added tributyl(vinyl)stannane (0.294 mL, 1.00 mmol), followed by bis(triphenylphosphine)palladium(II)chloride (0.029 g, 0.042 mmol) at room temperature. The reaction mixture was heated at 110° C. for 3 h. The reaction mixture was loaded onto a silica gel column and purified using hexane/EtOAc (9.25:0.75, 300 mL). The desired fractions were collected and concentrated to yield 0.35 mgs of a yellow solid. The solid was triturated with acetonitrile (5 mL), filtered and washed with acetonitrile (2×5 mL) to yield 200 mgs of a pale yellow solid (I crop). The mother liquor was concentrated to yield another 100 mgs of greenish-yellow solid (II crop). LC/MS M+1=425.

Workup

custompurified
customThe desired fractions were collected
concentrationconcentrated

Sources & evidence

ORD record: ord-3561ef5ca0a9453da1a53b9ee7c48399
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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